Ranking the Greats: The Films of Terry Gilliam

Ten terrific examples of how movies are magic from the only American member of Monty Python and a director worthy of the title "auteur".

Want to understand how horribly unjust the movie business is? Want a perfect example of creativity stifled by unrealistic commercial aims and even more perplexing professional bias? Terry Gilliam has been making movies for 35 years, and in that time, he’s managed a creative canon of ten. Ten. Compare that to someone like Shawn Levy (whose made the same number of films in a mere decade and a half) or Dennis Dugan (who Adam Sandler keeps hiring despite the fact that his 14 films in 23 years have failed as examples of entertainment or ability) and you can sense the cinephile outrage rising. As a member of the Monty Python troop, Gilliam gave us animated nightmares, his cut and paste perversions resulting in some of the series best moments. As a filmmaker, he’s crafted so many meaningful masterworks that, when something new is announced, fans automatically assume the best before (sometimes) receiving significantly less.

Now, nearly four years after his last movie, Gilliam has something new called The Zero Theorem, and thanks to the casting of two time Oscar winner Christoph Waltz, it already has Hollywood buzzing. A teaser trailer was “leaked” a while back, and that got us thinking about the filmmaker’s fascinating output overall. As a result, we’ve come up with our list of his best works, from ten to one. We have purposely left off any short film he’s done, as well as any documentary in which he is featured. We’ve also kept Monty Python and the Holy Grail out of the discussion since he was merely a co-director on it. Looking over the final placement, it’s clear that Gilliam’s original output was nothing short of magical. As the years and various disappointments piled on, his work became more erratic, and uneven. Still, even at his worst, the man is a master. Some studio should put him under contract and give him whatever money he wants (and final cut, of course) to make his movies commercial considerations be damned! He’s just that special. Let’s start at the bottom and work our way up.

#10 - The Brothers Grimm

This was supposed to be his late-in-coming breakout, the commercial film (with complete creative control) that would launch him from the obscurity of his considered cult to a massive mainstream audience. Heck, it has Matt Damon and Heath Ledger in the leads. But leave it to studio chief Harvey Weinstein to interfere where such fiddling was neither needed or wanted. He apparently placed so much pressure on Gilliam behind the scenes that the director felt “ridden roughshod” over. The results appeared up on the screen, an uneven bit of directorial brilliance and callous audience pandering. It made over $100 million at the box office, which would have been good, except for the $88 million budget spent.

#9 - Jabberwocky

After finishing up work on Monty Python and the Holy Grail (which he co-director with Terry Jones), Gilliam was anxious to get back behind the lens. So he drafted this nonsense monster movie with some cutting social satire and turned it into his first feature length solo outing. The reviews were mixed, but the end result indicated how far the filmmaker would go to establish his own voice in cinema. While his work with the Beatles of sketch comedy is hinted at here, so is a desire for period authenticity, outrageous spectacle, and the occasional lapse into scatology. A daft debut at best.

#8 - Tideland

Tideland is a tough cinematic nut to crack. There are actually two versions of the film, one released abroad in Gilliam’s approved aspect ratio, and the one offered to American audiences in a badly bugled 1.77:1 presentation. The filmmaker apparently hates the latter and went after it publicly in the PR push prior to the DVD release, which is not the best way to sell your wares. Let’s face it, however, this was always going to be a hard case, commercially. The story (from Mitch Cullin’s novel of the same name) centers on a young girl who loses her father to heroin addiction while befriending some true oddballs with their own troubling issues. Yikes.

#7 - The Imaginarium of Dr. Parnassus

Gilliam has never had luck as a filmmaker. His take on Don Quixote never got completed due to issues so surreal they became the basis for an entire documentary on the subject. Here, star Heath Ledger died before completing all his scenes, so the director called in favors from friends Johnny Depp, Colin Farrell, and Jude Law. They helped flesh out the missing material, adding another layer of unreality to a film already overflowing with Gilliam’s signature hallucinogens. The central theme, about aging and memory, is well encapsulated by star Christopher Plummer while the rest of the movie plays like a mockery of all those silly self help guides.

#6 - The Fisher King

From 1988 to 1998, Gilliam made five amazing masterpieces. This is the one that has aged the worst. There is just something sadly dated about the shock jock antics of Jeff Bridges’ character, as well as the novelty of his defeated celebrity working at a video store. Still, this is a positively poetic look at life and second chances, perhaps best exemplified by Robin Williams’ insane homeless man character. Once we learn the truth of what happened to him, and how Bridges is connected to same, we see the message Gilliam meant and how intoxicating it is. A beautiful and often heartbreaking film.